End of Quarter (Century) Thoughts

I’m writing this a few weeks after my 26th birthday. It’s a year later than I intended to write it, but so much has happened this past year that I’m glad I waited.

The cottage industry of internet self-help gurus is ripe with people pushing hot-take content in various forms across all media. These are the guys and girls with four or five self-given titles like innovator, visionary, and entrepreneur. There’s even a Udemy course on how to be one of these people yourself. Some of these people are actually the things that they purport to be, but most are exploiting a just-beyond-nascent market where the bar to entry is low and the imposters are copious.

I’m not trying to enter that market and my blog definitely isn’t going in that direction. However, I am going to lay out a few things I’ve learned over the past years.

The act of recording them here for my own future reference and reflection is as important to me as sharing them.

None of the below are highly prescriptive; they are simply principles that I’ve codified over the past couples years and will continue to expand upon going forward.

A small amount of words and numbers carefully chosen is vastly more effective than a large amount of either in isolation

Most people fall into one of two categories: they are good either with numbers or words. There is no issue with specializing in either of those two things, and you can make an incredible career by being talented with either.

The issue isn’t with your output, though. It’s with the audience for your work. A large block of text tunes out as many people as a page filled with numbers. Just as a deft blog post can convey an idea as well as a long tome, so too can an elegant figure share the same quality of idea as a lengthy proof.

In and out of the office, the best presentations and ideas make sure-footed use of deliberate numbers with choice word highlights. Those who can best synthesize the two are at a considerable advantage to those who specialize.

Observing is understanding is conquering

There are times when it is best to learn by doing and there are times when you just need to shut up and listen. It’s important to learn to spot when you should do one or the other.

I had the chance to interview Intercom’s CEO Eoghan McCabe in front of our sales team at Intercom’s global sales kick-off two weeks ago. One of the questions I posed to him was something along the lines of: “There are many people in the room who want to be future leaders both here at Intercom and in their own companies. What advice do you have for them?”

He made a number of good points and also highlighted the characteristics that stand out to him in particular. His words – and I’m paraphrasing here – were ‘a quiet confidence and sharp listening skills are among the most effective skills someone can develop.’

That internal confidence and the ability to learn from observation create a very strong positive feedback loop.

You prove yourself by how you act during the down days

We are in an extended 9+ year stock market run and have reached unprecedented levels of wealth and prosperity. There are a full 7-10 years of people entering the workforce who weren’t financially literate during the Great Recession. There is more money in the system now than ever before (yes, I’m conflating fiat with dry powder). That money is currently finding a place to go to work, which means that ideas are being funded which probably wouldn’t in a more cautious time period.

This is more than ‘everyone is a genius in a bull market’ and ‘only when the tide goes out do you discover who’s been swimming naked.’ It’s more that there are a lot of people out there who haven’t really felt failure on any grand scale. I’m not asking to be a martyr for those who have, but I do want to call attention to the lack of mental models in place for when a downturn does eventually happen.

It takes less practice to get good at dealing with success than it does to get good at dealing with failure. Your reputation is made on the days when you are presented with failure and are forced to deal with it in full view of everyone around you.

Develop and refine your thesis early

A lot of people have made a lot of money by developing a thesis early. They may refine it over time, but they never stray too far from their initial idea. The best thesis isn’t a set of rules but rather a flexible grouping of principles (like this post!).

Union Square Ventures (USV) is one of the best examples of a fund which has had outsized success sticking to a core thesis. You can read about this thesis on USV’s website here and here, but USV partner Brad Burnham sums this up well in the tweet below:

USV in 140 characters: invest in large networks of engaged users, differentiated by user experience, and defensible though network effects

USV is an example of a firm that has succeeded by developing, revising, and adhering to a core set of beliefs about how the world works. It’s equally as effective and beneficial to do this in your personal life, too.

Develop your thesis about what types of companies you want to work for, what type of people you want to be around, what types of relationships you want to have. Revise it over time. But do it early! The earlier you start, the more refined and capable you’ll be 10 years from now. See ‘Observing is…’ above.

Find work where you get the most satisfaction and enjoyment out of the feeling you get when you succeed in that area

I’ve found that the times when I am most happy at work are when I am busiest. There’s nothing quite like the combined feeling of being in the zone and in your element.

We are all working for the moments when we have great success (and preparing ourselves for when we have the greatest failures – see below). But, like Meek said, there are levels to this. You can find easy success in any number of places, but the hardest successes are the most rewarding. There’s a third axis to that relationship, though, which is the internal satisfaction you get from that success. This is a bit more intangible, but I promise that you’ll know it when you feel it. Long-term happiness at work comes from achieving local maxima with respect to those factors while moving into increasingly challenging roles.

Take a guess at a career out of college and go do it

You probably won’t be right, but that doesn’t matter. The only way you’ll ever know what you’re supposed to do is by failing. The only mistake you can make in choosing your first job is to be passive instead of active.

Have you ever seen one of those videos of a machine learning model teaching itself to play a video game? The training model makes the character awkwardly crash and bump up against objects in the environment:

When you graduate school, you are that untrained model. You need to break things and crash a few times to learn about your environment and the character you are controlling. You’re going to look like this at a few points:

But you’ll gradually get better. Learning what you don’t want to do is a necessary step to learning what you truly want to do. Develop your thesis!

Define your circle of competence

Despite any efforts to the contrary, every action you take affects what others think of you. People refer to this as a personal brand (FWIW, anyone who talks about their personal brand is a total square).

I instead try to think of my circle of competence. This is the core set of skills and tools that I can fall back on. You’ll always be pushing to develop new skills and push yourself, but your core competencies are always there when all else fails.

At work, your core competencies are the first principles layer of your personal brand.

Take all advice with a grain of salt

Especially posts like these. These are what have worked for me, but they could be very far off from what works for you.

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This blog is where I write about tech, ideas, and whatever else interests me. Once every few weeks or so. It’s my outlet for exploring concepts and improving my writing. The views expressed here are my own and do not reflect those of my employer.

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